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Gold-Catalyzed Anti-Markovnikov Oxidation of Au-Allenylidene to Generate Alkylidene Ketene

Xinhao Sun, Xuelun Duan, Nan Zheng* and Wangze Song*

*School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. China, Email:,

X. Sun, X. Duan, N. Zheng, W. Song, Org. Lett., 2023, 25, 2798-2805.

DOI: 10.1021/acs.orglett.3c00682

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A unique Au-allenylidene pathway enables an in situ formation of highly unsaturated alkylidene ketenes from propargyl alcohol derivatives. A subsequent trapping with a broad range of nucleophiles such as alcohols, phenols, water, amines, and sulfoximines in the presence of an N-oxide provides α,β-unsaturated drug and natural product derivatives.

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proposed mechanism

Key Words

oxidation, unsaturated esters, multicomponent reaction, pyridine N-oxides

ID: J54-Y2023